The purpose of the present study was to extend the research on the Psychology of Working Theory (PWT; Duffy, Blustein, Diemer, & Autin, 2016) by testing its applicability to workers with chronic health conditions. Specifically, we examined the PWT's posited predictors of securing decent work in a sample of 320 workers diagnosed with Chiari malformation-Type 1 (CM). Results of structural equation modeling analyses supported 8 of the 14 hypothesized relations. Notably, economic constraints and marginalization significantly and inversely predicted decent work and work volition; economic constraints significantly and inversely predicted career adaptability, which in turn significantly and positively predicted decent work; and career adaptability partially explained the significant relation of economic constraints to decent work. Collectively, our findings provided strong support for the applicability of the PWT for workers diagnosed with CM. We offer several directions for future research on the PWT and the work lives of persons living with CM.